The 4 Ballsiest Career Moves by Famous Musicians

There are some moments in popular music that everyone recognizes as watershed events. Times when artists made counterintuitive decisions that were hailed as brave, bold, and influential. In 1967, when the Beatles emerged from Abbey Road Studios with Sgt. Pepper -- a perfect album of pop, rock, and psychedelia unlike anything they or anyone else had made before -- the world stood up and recognized. When Bob Dylan, the leading force of the folk movement, went electric at Newport in 1965, people marveled at his audacity.

Rolling StoneThey also would have marveled at his amazing neon green jacket, but the world was in black and white in 1965 (as shown here)
and no one could tell.

And the world was right. These were important artists with huge followings who had no need to change course or rock the boat. They pursued new ideas when no one asked them to and gave us something worthwhile with their exploration. But there are a handful of quieter moments in music where artists required huge balls to do certain things that people either don't remember or just never classified as brave. Subtler acts of ballsy greatness. Here are four of my favorites.

#4. David Bowie Sets Himself Up for Failure, Alienating a Diverse Audience in 1995 With Some of His Best Work

David Bowie has had a 40-year career in music, the majority of which was spent bucking convention. But that's not why he's in this article. After all, people always talk about the chances Bowie's taken in his career: leaving the success of glam to pursue soul, leaving soul to pursue minimalism and electronica, leaving minimalism and electronica to pursue full-blown pop stardom, and rejecting all that stardom as part of a deliberately pop-unfriendly band, Tin Machine. That's all old news. In fact, you've probably seen cheesy news or Internet segments flashing pics from all of these periods at high speed over Bowie's song "Changes." I was going to embed one of them here, but they're all lame. Here's some great early Bowie instead:

But a career dedicated to individuality and integrity is not what gets you onto this list. If it were, Frank Zappa would have to be here, too. This is a list about seldom-discussed single acts of musical bravery, and for that we have to go to New York in 1995.

Bowie spent the first half of the '90s trying to kill off the pop music fan base he'd acquired in the '80s with Let's Dance and Labyrinth. By 1995, he had done so, and he re-emerged with the incredibly strong and sonically demanding Outside album, produced by his former collaborator Brian Eno. He also teamed up with Trent Reznor and went on tour with Nine Inch Nails at the height of NIN's popularity. Furthermore, the shows were continuous, with the two artists slowly integrating their bands. The show went NIN, NIN plus Bowie, NIN plus Bowie and his band, Bowie and his band plus just Reznor, and then just Bowie and his band for the rest of his show. Got it?

At that precise moment in time, NIN was a much bigger draw than Bowie, but because Trent Reznor is not a disrespectful prick, he rightly allowed Bowie a slightly more exalted position on the bill. Here's the deal, though. The overwhelming majority of the coliseum was there to see NIN. The audience was awash with 14-year-old girls in torn fishnets and black lipstick. Even though they probably went off to college, broadened their musical horizons, and became Bowie fans (considering what a huge NIN influence he is), on that night, they were not. But it gets worse. The Outside album is dense, difficult, and over 70 minutes long. Also, it was released the day before the concert, and Bowie played almost exclusively from it. Accordingly, even the minority of the crowd who was there for Bowie did not know what the hell he was playing. Even I had only heard it all the way through a half-dozen times before the show.

When Trent left the stage, so did half the audience, some of them crying that they didn't get enough Trent. Bowie "ruined the show" for them. (That's an actual quote from some girl I overheard in the parking lot ... moments before I strangled her to death.) So many people left that they let my friends and me fill the empty spot before the stage, and I watched the show literally 10 feet from Bowie. And I felt like the only person in the entire place who enjoyed it.

Let's recap: Bowie plays to one of the largest venues in New York, goes onstage with someone far more popular than he at that specific moment in time, and plays to the other guy's audience. Then he plays only demanding music that his own audience does not know. Bowie played great and tanked. He knew he would. How could he not? And he just didn't care. He did what he wanted to do, able to withstand a stadium's worth of undeserved antipathy and indifference. Some people think it's brave that I read the comments to what I write online. I'm not sure "brave" is a good explanation. I read comments for every reason from narcissism to practicality to masochism, but if there is anything brave about it, it comes from Bowie. More than at any other time in his career, Bowie was my hero that night. Putting himself into the mix in the exact way he wanted, hoping to be appreciated, but not depending upon it. Not having his sense of self shaken. When it was over, he said simply, "Well, you've been very kind to listen to so many songs you don't know. Here's one you do." And then closed with "Under Pressure" with the incomparable Gail Ann Dorsey playing bass and killing Freddie Mercury's parts.

#3. Lisa Germano Shows How Badass She Is by NOT Being a Tough Grrl

Hey guys, remember Lisa Germano? No? Oh. Well, she spent the majority of her career playing fiddle in John Mellencamp's band. Here she is hoedowning it up during "Paper in Fire":

In 1993, Germano released her own solo album. That's not surprising. Lots of women started singer-songwriter careers in the '90s. The record companies were signing everyone in support of the then popular Lilith Fair festival. Tori Amos, Sarah McLachlan, Shawn Colvin, Fiona Apple, Paula Cole, and Meredith Brooks were all in the air and all over the radio. And in my super politically correct Northeast liberal arts college, women were reading Naomi Wolf's The Beauty Myth and wondering if giving head would make them a member of an oppressed class.

Paula Cole touted her unshaved pits. Tori Amos and Sarah McLachlan sang about rape and stalkers. Meredith Brooks told us what a bitch she was, and Jill Sobule let everyone know that she kissed a girl and was like totally OK with it. Clearly, the key to success was to release music adhering to the then omnipresent theme of grrl power. And into that mix, Lisa Germano releases "You Make Me Want to Wear Dresses":

A simple, catchy tune about how her love makes her feel all girly and gives her the desire to embrace traditional roles. Releasing this song in 1993 would be the equivalent of some LA-based rap group following NWA's "Fuck Tha Police" with "Thank You for Keeping Our Neighborhood Safe, Officer."

No one cares about the song. It didn't do well or establish a brand new solo career, but it bucked all calculating conventional wisdom in the air at that time. It was the song she wanted to make, and she made it, and I can't think of any definition of being empowered beyond that.